WO2019235803A1 - Composé électroluminescent organique et dispositif électroluminescent organique le comprenant - Google Patents

Composé électroluminescent organique et dispositif électroluminescent organique le comprenant Download PDF

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WO2019235803A1
WO2019235803A1 PCT/KR2019/006700 KR2019006700W WO2019235803A1 WO 2019235803 A1 WO2019235803 A1 WO 2019235803A1 KR 2019006700 W KR2019006700 W KR 2019006700W WO 2019235803 A1 WO2019235803 A1 WO 2019235803A1
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substituted
unsubstituted
organic electroluminescent
alkyl
compound
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PCT/KR2019/006700
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English (en)
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Hyun-Ju Kang
Hyo-Jung Lee
Sung-Wook Cho
Sang-Hee Cho
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Rohm And Haas Electronic Materials Korea Ltd.
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Priority to CN201980031791.5A priority Critical patent/CN112119139A/zh
Publication of WO2019235803A1 publication Critical patent/WO2019235803A1/fr

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    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
    • C09K11/00—Luminescent, e.g. electroluminescent, chemiluminescent materials
    • C09K11/06—Luminescent, e.g. electroluminescent, chemiluminescent materials containing organic luminescent materials
    • H—ELECTRICITY
    • H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
    • H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
    • H10K50/00—Organic light-emitting devices
    • H10K50/10—OLEDs or polymer light-emitting diodes [PLED]
    • H10K50/11—OLEDs or polymer light-emitting diodes [PLED] characterised by the electroluminescent [EL] layers
    • H—ELECTRICITY
    • H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
    • H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
    • H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
    • H10K85/60—Organic compounds having low molecular weight
    • H10K85/649—Aromatic compounds comprising a hetero atom
    • H10K85/654—Aromatic compounds comprising a hetero atom comprising only nitrogen as heteroatom
    • H—ELECTRICITY
    • H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
    • H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
    • H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
    • H10K85/60—Organic compounds having low molecular weight
    • H10K85/649—Aromatic compounds comprising a hetero atom
    • H10K85/657—Polycyclic condensed heteroaromatic hydrocarbons
    • H10K85/6572—Polycyclic condensed heteroaromatic hydrocarbons comprising only nitrogen in the heteroaromatic polycondensed ring system, e.g. phenanthroline or carbazole
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
    • C09K2211/00—Chemical nature of organic luminescent or tenebrescent compounds
    • C09K2211/10—Non-macromolecular compounds
    • C09K2211/1018—Heterocyclic compounds
    • C09K2211/1025—Heterocyclic compounds characterised by ligands
    • C09K2211/1044—Heterocyclic compounds characterised by ligands containing two nitrogen atoms as heteroatoms
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
    • C09K2211/00—Chemical nature of organic luminescent or tenebrescent compounds
    • C09K2211/10—Non-macromolecular compounds
    • C09K2211/1018—Heterocyclic compounds
    • C09K2211/1025—Heterocyclic compounds characterised by ligands
    • C09K2211/1059—Heterocyclic compounds characterised by ligands containing three nitrogen atoms as heteroatoms
    • H—ELECTRICITY
    • H01—ELECTRIC ELEMENTS
    • H01G—CAPACITORS; CAPACITORS, RECTIFIERS, DETECTORS, SWITCHING DEVICES OR LIGHT-SENSITIVE DEVICES, OF THE ELECTROLYTIC TYPE
    • H01G9/00—Electrolytic capacitors, rectifiers, detectors, switching devices, light-sensitive or temperature-sensitive devices; Processes of their manufacture
    • H01G9/20—Light-sensitive devices
    • H01G9/2004—Light-sensitive devices characterised by the electrolyte, e.g. comprising an organic electrolyte
    • H01G9/2013—Light-sensitive devices characterised by the electrolyte, e.g. comprising an organic electrolyte the electrolyte comprising ionic liquids, e.g. alkyl imidazolium iodide
    • H—ELECTRICITY
    • H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
    • H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
    • H10K2101/00—Properties of the organic materials covered by group H10K85/00
    • H10K2101/10—Triplet emission
    • H—ELECTRICITY
    • H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
    • H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
    • H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
    • H10K85/60—Organic compounds having low molecular weight
    • H10K85/649—Aromatic compounds comprising a hetero atom
    • H10K85/657—Polycyclic condensed heteroaromatic hydrocarbons
    • H10K85/6574—Polycyclic condensed heteroaromatic hydrocarbons comprising only oxygen in the heteroaromatic polycondensed ring system, e.g. cumarine dyes

Definitions

  • the present disclosure relates to an organic electroluminescent compound and an organic electroluminescent device comprising the same.
  • An electroluminescent device is a self-light-emitting display device which has advantages in that it provides a wider viewing angle, a greater contrast ratio, and a faster response time.
  • the first organic EL device was developed by Eastman Kodak in 1987, by using small aromatic diamine molecules and aluminum complexes as materials for forming a light-emitting layer [Appl. Phys. Lett. 51, 913, 1987].
  • An organic EL device changes electric energy into light by applying electricity to an organic electroluminescent material, and commonly comprises an anode, a cathode, and an organic layer formed between the two electrodes.
  • the organic layer of the organic EL device may comprise a hole injection layer, a hole transport layer, a hole auxiliary layer, a light-emitting auxiliary layer, an electron blocking layer, a light-emitting layer (containing host and dopant materials), an electron buffer layer, a hole blocking layer, an electron transport layer, an electron injection layer, etc.
  • organic EL device holes from the anode and electrons from the cathode are injected into a light-emitting layer by the application of an electric voltage, and excitons having high energy are produced by the recombination of the holes and electrons.
  • the organic light-emitting compound moves into an excited state by the energy and emits light from an energy when the organic light-emitting compound returns to the ground state from the excited state.
  • CBP 4,4’-N,N’-dicarbazol-biphenyl
  • CBP 4,4’-N,N’-dicarbazol-biphenyl
  • the conventional phosphorescent host materials provide good luminous characteristics, they have the following disadvantages: (1) Due to their low glass transition temperature and poor thermal stability, their degradation may occur during a high-temperature deposition process in a vacuum, and the lifespan of the device may be shortened. (2) The power efficiency of the organic electroluminescent device is given by [( ⁇ /voltage) ⁇ current efficiency], and the power efficiency is inversely proportional to the voltage.
  • the organic electroluminescent device comprising phosphorescent host materials provides higher current efficiency (cd/A) than one comprising fluorescent materials, a significantly high driving voltage is necessary.
  • the materials constituting the organic layer in the device, in particular, the host or dopant constituting the light-emitting material, sholud be appropriately selected.
  • Korean Patent No. 2014-0006708 A discloses an organic electroluminescent device using a compound as a green phosphorescent host material in that a pyridine, pyrimidine or triazine is linked to an indolocarbazole derivative using at least one naphthylene as a linker.
  • Korean Patent Nos. 2013-0057397 A and 2016-0131963 A disclose a heterocyclic compound which can be used as a host material for a light-emitting layer; however, they do not disclose a host compound having an indolocarbazole derivative as a basic skeleton.
  • the object of the present disclosure is firstly, to provide an organic electroluminescent compound which is able to produce an organic electroluminescent device having low driving voltage and/or high luminous efficiency, and/or long lifespan, and secondly, to provide an organic electroluminescent device comprising the organic electroluminescent compound.
  • a ring is tri- or more cyclic ring
  • Ar1 and Ar2 each independently represent hydrogen, deuterium, cyano, a substituted or unsubstituted (C1-C30)alkyl, a substituted or unsubstituted (C6-C30)aryl, a substituted or unsubstituted (3- to 30-membered)heteroaryl, or a substituted or unsubstituted (C3-C30)cycloalkyl;
  • L 1 and L 2 each independently represent a single bond, a substituted or unsubstituted (C1-C30)alkylene, a substituted or unsubstituted (C6-C30)arylene, a substituted or unsubstituted (3- to 30-membered)heteroarylene, or a substituted or unsubstituted (C3-C30)cycloalkylene;
  • R 1 to R 3 each independently represent hydrogen, deuterium, halogen, cyano, a substituted or unsubstituted (C1-C30)alkyl, a substituted or unsubstituted (C6-C30)aryl, a substituted or unsubstituted (3- to 30-membered)heteroaryl, a substituted or unsubstituted (C3-C30)cycloalkyl, a substituted or unsubstituted (C1-C30)alkoxy, a substituted or unsubstituted tri(C1-C30)alkylsilyl, a substituted or unsubstituted di(C1-C30)alkyl(C6-C30)arylsilyl, a substituted or unsubstituted (C1-C30)alkyldi(C6-C30)arylsilyl, a substituted or unsubstituted tri(C6-C30)aryl
  • a represents an integer of 1 to 4.
  • b represents an integer of 1 or more
  • c represents an integer of 1 or 2;
  • each of R 1 , each of R 2 , or each of R 3 may be the same or different.
  • an organic electroluminescent device having a low driving voltage and/or a high luminous efficiency and/or long lifespan can be prepared.
  • the present disclosure relates to an organic electroluminescent compound represented by formula 1 and an organic electroluminescent device comprising the organic electroluminescent compound.
  • organic electroluminescent compound in the present disclosure means a compound that may be used in an organic electroluminescent device, and may be comprised in any material layer constituting an organic electroluminescent device, as necessary.
  • organic electroluminescent material in the present disclosure means a material that may be used in an organic electroluminescent device, and may comprise at least one compound.
  • the organic electroluminescent material may be comprised in any layer constituting an organic electroluminescent device, as necessary.
  • the organic electroluminescent material may be a hole injection material, a hole transport material, a hole auxiliary material, a light-emitting auxiliary material, an electron blocking material, a light-emitting material, an electron buffer material, a hole blocking material, an electron transport material, or an electron injection material, etc.
  • (C1-C30)alkyl(ene) is meant to be a linear or branched alkyl having 1 to 30 carbon atoms constituting the chain, in which the number of carbon atoms is preferably 1 to 20, and more preferably 1 to 10.
  • the above alkyl may include methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, tert-butyl, etc.
  • “(C3-C30)cycloalkyl(ene)” is a mono- or polycyclic hydrocarbon having 3 to 30 ring backbone carbon atoms, in which the number of carbon atoms is preferably 3 to 20, and more preferably 3 to 7.
  • cycloalkyl may include cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, etc.
  • (C6-C30)aryl(ene) is a monocyclic or fused ring radical derived from an aromatic hydrocarbon having 6 to 30 ring backbone carbon atoms, in which the number of the ring backbone carbon atoms is preferably 6 to 20, more preferably 6 to 15, may be partially saturated, and may comprise a spiro structure.
  • aryl specifically include phenyl, biphenyl, terphenyl, quaterphenyl, naphthyl, binaphthyl, phenylnaphthyl, naphthylphenyl, fluorenyl, phenylfluorenyl, dimethylfluorenyl, diphenylfluorenyl, benzofluorenyl, diphenylbenzofluorenyl, dibenzofluorenyl, phenanthrenyl, benzophenanthrenyl, phenylphenanthrenyl, anthracenyl, benzanthracenyl, indenyl, triphenylenyl, pyrenyl, tetracenyl, perylenyl, chrysenyl, benzochrysenyl, naphthacenyl, fluoranthenyl, benzofluoranthenyl, tolyl, xylyl, me
  • the aryl may be o-tolyl, m-tolyl, p-tolyl, 2,3-xylyl, 3,4-xylyl, 2,5-xylyl, mesityl, o-cumenyl, m-cumenyl, p-cumenyl, p-t-butylphenyl, p-(2-phenylpropyl)phenyl, 4'-methylbiphenyl, 4"-t-butyl-p-terphenyl-4-yl, o-biphenyl, m-biphenyl, p-biphenyl, o-terphenyl, m-terphenyl-4-yl, m-terphenyl-3-yl, m-terphenyl-2-yl, p-terphenyl-4-yl, p-terphenyl-3-yl, p-terphenyl-2-yl, p-terphenyl-4-
  • (3- to 30-membered)heteroaryl(ene) is an aryl having 3 to 30 ring backbone atoms, in which the number of ring backbone atoms is preferably 5 to 25, including at least one, preferably 1 to 4 heteroatoms selected from the group consisting of B, N, O, S, Si, P, and Ge.
  • the above heteroaryl may be a monocyclic ring, or a fused ring condensed with at least one benzene ring; and may be partially saturated.
  • the above heteroatom may be linked with at least one substituent selected from the group consisting of hydrogen, deuterium, halogen, cyano, a substituted or unsubstituted (C1-C30)alkyl, a substituted or unsubstituted (C6-C30)aryl, a substituted or unsubstituted (5- to 30-membered)heteroaryl, a substituted or unsubstituted (C3-C30)cycloalkyl, a substituted or unsubstituted (C1-C30)alkoxy, a substituted or unsubstituted tri(C1-C30)alkylsilyl, a substituted or unsubstituted di(C1-C30)alkyl(C6-C30)arylsilyl, a substituted or unsubstituted (C1-C30)alkyldi(C6-C30)arylsilyl, a substituted or unsubstit
  • the above heteroaryl may be one formed by linking at least one heteroaryl or aryl group to a heteroaryl group via a single bond(s); and may comprise a spiro structure.
  • the heteroaryl specifically may include a monocyclic ring-type heteroaryl including furyl, thiophenyl, pyrrolyl, imidazolyl, pyrazolyl, thiazolyl, thiadiazolyl, isothiazolyl, isoxazolyl, oxazolyl, oxadiazolyl, triazinyl, tetrazinyl, triazolyl, tetrazolyl, furazanyl, pyridyl, pyrazinyl, pyrimidinyl, pyridazinyl, etc., and a fused ring-type heteroaryl including benzofuranyl, benzothiophenyl, isobenzofuranyl, dibenzofuranyl, dibenzothioph
  • the heteroaryl may be 1-pyrrolyl, 2-pyrrolyl, 3-pyrrolyl, 2-pyridinyl, 3-pyridinyl, 4-pyridinyl, 2-pyrimidinyl, 4-pyrimidinyl, 5-pyrimidinyl, 6-pyrimidinyl, 1,2,3-triazin-4-yl, 1,2,4-triazin-3-yl, 1,3,5-triazin-2-yl, 1-imidazolyl, 2-imidazolyl, 1-pyrazolyl, 1-indolizidinyl, 2-indolizidinyl, 3-indolizidinyl, 5-indolizidinyl, 6-indolizidinyl, 7-indolizidinyl, 8-indolizidinyl, 2-imidazopyridinyl, 3-imidazopyridinyl, 5-imidazopyridinyl, 6-imidazopyridinyl, 7-imidazopyridinyl, 8-imidazopyridiny
  • Nonrogen-containing (5- to 30-membered)heteroaryl(ene) is meant to be an aryl group having at least one N, and 5 to 30 ring backbone atoms, in which the number of ring backbone atoms is preferably 5 to 20, more preferably 5 to 15; having preferably 1 to 4 heteroatoms, and may be a monocyclic ring, or a fused ring condensed with at least one benzene ring; may be partially saturated.
  • the above nitrogen-containing heteroaryl may be one formed by linking at least one heteroaryl or aryl group to a heteroaryl group via a single bond(s); and includes a monocyclic ring-type heteroaryl including pyrrolyl, imidazolyl, pyrazolyl, triazinyl, tetrazinyl, triazolyl, tetrazolyl, pyridyl, pyrazinyl, pyrimidinyl, pyridazinyl, etc., and a fused ring-type heteroaryl including benzimidazolyl, isoindolyl, indolyl, indazolyl, benzothiadiazolyl, quinolyl, isoquinolyl, cinnolinyl, quinazolinyl, quinoxalinyl, benzoquinoxalinyl, carbazolyl, phenanthridinyl, etc.
  • "Halogen" includes F, Cl, Br
  • Ortho position is a compound with substituents, which are adjacent to each other, e.g., at the 1 and 2 positions on benzene.
  • Meta position is the next substitution position of the immediately adjacent substitution position, e.g., a compound with substituents at the 1 and 3 positions on benzene.
  • Para position is the next substitution position of the meta position, e.g., a compound with substituents at the 1 and 4 positions on benzene.
  • a substituted or unsubstituted ring formed in linked to an adjacent substituent means a substituted or unsubstituted (C3-C30) mono- or polycyclic, alicyclic, aromatic ring, or a combination thereof, formed by linking or fusing two or more adjacent substituents; preferably, may be a substituted or unsubstituted (C5-C25) mono- or polycyclic, alicyclic, aromatic ring, or a combination thereof; more preferably, may be a substituted or unsubstituted (C5-C18) mono- or polycyclic, alicyclic, aromatic ring, or a combination thereof.
  • At least one of the carbon atoms in the formed ring may be replaced with at least one heteroatom selected from the group consisting of B, N, O, S, Si, and P, preferably, N, O, and S.
  • the ring formed in linking to an adjacent substituent may be a (C5-C20) polycyclic aromatic ring, which may contain at least one heteroatom selected from the group consisting of N, O, and S.
  • substituted in the expression “substituted or unsubstituted” means that a hydrogen atom in a certain functional group is replaced with another atom or functional group, i.e., a substituent.
  • the organic electroluminescent compound according to one embodiment is represented by the following formula 1.
  • a ring is a tri- or more cyclic ring
  • Ar1 and Ar2 each independently represent hydrogen, deuterium, cyano, a substituted or unsubstituted (C1-C30)alkyl, a substituted or unsubstituted (C6-C30)aryl, a substituted or unsubstituted (3- to 30-membered)heteroaryl, or a substituted or unsubstituted (C3-C30)cycloalkyl;
  • L 1 and L 2 each independently represent a single bond, a substituted or unsubstituted (C1-C30)alkylene, a substituted or unsubstituted (C6-C30)arylene, a substituted or unsubstituted (3- to 30-membered)heteroarylene, or a substituted or unsubstituted (C3-C30)cycloalkylene;
  • R 1 to R 3 each independently represent hydrogen, deuterium, halogen, cyano, a substituted or unsubstituted (C1-C30)alkyl, a substituted or unsubstituted (C6-C30)aryl, a substituted or unsubstituted (3- to 30-membered)heteroaryl, a substituted or unsubstituted (C3-C30)cycloalkyl, a substituted or unsubstituted (C1-C30)alkoxy, a substituted or unsubstituted tri(C1-C30)alkylsilyl, a substituted or unsubstituted di(C1-C30)alkyl(C6-C30)arylsilyl, a substituted or unsubstituted (C1-C30)alkyldi(C6-C30)arylsilyl, a substituted or unsubstituted tri(C6-C30)aryl
  • a represents an integer of 1 to 4.
  • b represents an integer of 1 or more
  • c represents an integer of 1 or 2;
  • each of R 1 , each of R 2 , or each of R 3 may be the same or different.
  • the organic electroluminescent compound of formula 1 may be comprised in the light-emitting layer of an organic electroluminescent device as host materials.
  • the organic electroluminescent compound of formula 1 has a basic skeleton in which an electron withdrawing group (EWG) having high electron withdrawing ability such as an aryl group and/or a nitrogen-containing heteroaryl group is bonded to an indolocarbazole derivative.
  • EWG electron withdrawing group
  • indolocarbazole can be formed as various structures according to the linking position of a carbazole moiety and is suitable to use in a hole transport host due to high HOMO (Highest Occupied Molecular Orbital) energy level.
  • the organic electroluminescent compound of formula 1 is a structure in which nitrogen (N) of indolocarbazole is bonded in a specific direction, i.e., to face in the same direction; and an indolocarbazole condensed with at least one benzene ring at its terminal, as a basic skeleton; a nitrogen(s) (N) of indolocarbazole is bonded to an aryl group having a strong electron characteristic and/or a nitrogen-containing heteroaryl group, thereby the entire molecule thereof has bipolar characteristics.
  • the bonding force between the hole and the electron can be increased, so that the compound of the present disclosure can exhibit excellent characteristics as a host material of the light-emitting layer; and as a result, an organic electroluminescent device having a low driving voltage and/or a high luminous efficiency and/or long lifespan can be provided.
  • the structure in which at least one benzene ring is condensed with the indolocarbazole moiety enhances the thermal stability of the device due to increasing the conjugation length while maintaining the properties of the material, thereby improving the lifespan characteristics.
  • a ring is a tri- or more cyclic ring, e.g., may be tricyclic to pentacyclic ring.
  • a ring may be a tri- or more cyclic aryl ring, more preferably, a condensed ring condensed with at least three benzene rings.
  • a ring may be a substituted or unsubstituted phenanthrene, or a substituted or unsubstituted phenalene.
  • the organic electroluminescent compound according to one embodiment may be represented by any one of the following formulae 1-1 to 1-3, as a basic skeleton in which at least one benzene ring is condensed with indolo[2,3-b]carbazole moiety.
  • Ar1, Ar2, L 1 , L 2 , R 1 to R 3 , a and c are defined as formula 1;
  • R 4 and R 5 each independently represent, hydrogen, deuterium, halogen, cyano, a substituted or unsubstituted (C1-C30)alkyl, a substituted or unsubstituted (C6-C30)aryl, a substituted or unsubstituted (3- to 30-membered)heteroaryl, a substituted or unsubstituted (C3-C30)cycloalkyl, a substituted or unsubstituted (C1-C30)alkoxy, a substituted or unsubstituted tri(C1-C30)alkylsilyl, a substituted or unsubstituted di(C1-C30)alkyl(C6-C30)arylsilyl, a substituted or unsubstituted (C1-C30)alkyldi(C6-C30)arylsilyl, a substituted or unsubstituted tri(C6-C30)ary
  • b represents an integer of 1 to 6;
  • d and e each independently are defined as a;
  • each of R 2 , each of R 4 , or each of R 5 may be the same or different.
  • Ar1 and Ar2 each independently represent hydrogen, deuterium, cyano, a substituted or unsubstituted (C1-C30)alkyl, a substituted or unsubstituted (C6-C30)aryl, a substituted or unsubstituted (3- to 30-membered)heteroaryl, or a substituted or unsubstituted (C3-C30)cycloalkyl, preferably, each independently may be hydrogen, a substituted or unsubstituted (C6-C18)aryl or a substituted or unsubstituted (3- to 18-membered)heteroaryl, more preferably, each independently may be hydrogen, a substituted or unsubstituted (C6-C12)aryl, or a substituted or unsubstituted nitrogen-containing (5- to 20-membered) heteroaryl.
  • Ar1 and Ar2 each independently may be hydrogen, a substituted or unsubstituted phenyl, a substituted or unsubstituted o-biphenyl, a substituted or unsubstituted m-biphenyl, a substituted or unsubstituted p-biphenyl, a substituted or unsubstituted naphthyl, a substituted or unsubstituted triphenyl, a substituted or unsubstituted triazinyl, a substituted or unsubstituted quinoxalinyl, a substituted or unsubstituted quinazolinyl, or a substituted or unsubstituted benzoquinoxalinyl.
  • a nitrogen(s) of indolocarbazole moiety is(are) bonded to an aryl group having a strong electron characteristic and/or a nitrogen-containing heteroaryl group; preferably at least one nitrogen of indolocarbazole moiety may be bonded to a nitrogen-containing heteroaryl group.
  • the selection of substituents having a suitable electron-transporting property is important since the band gap, electrical characteristics, interface characteristics, etc., may be changed according to the type of substituent and the bonding position.
  • Ar1 and Ar2 each independently may be a nitrogen-containing heteroaryl selected from the following formulae 2-1 and 2-2. Thereby, the lifespan of an organic electroluminescent device comprising the organic electroluminescent compound according to one embodiment can be improved.
  • X each independently represents N or CR 21 ;
  • R 11 and R 21 each independently represent hydrogen, deuterium, cyano, a substituted or unsubstituted (C1-C30)alkyl, a substituted or unsubstituted (C6-C30)aryl, or a substituted or unsubstituted (3- to 30-membered)heteroaryl; or may be linked to adjacent substituents to form a substituted or unsubstituted ring; and
  • n an integer of 1 to 4.
  • At least one X may be N, for example, at least two X may be N.
  • Ar1 or Ar2 represented by formula 2-1 may be a substituted or unsubstituted triazinyl
  • Ar1 or Ar2 represented by formula 2-2 may be a substituted or unsubstituted naphthyl, a substituted or unsubstituted quinoxalinyl, a substituted or unsubstituted quinazolinyl, or a substituted or unsubstituted benzoquinoxalinyl.
  • L 1 and L 2 each independently represent, a single bond, a substituted or unsubstituted (C1-C30)alkylene, a substituted or unsubstituted (C6-C30)arylene, a substituted or unsubstituted (3- to 30-membered)heteroarylene, or a substituted or unsubstituted (C3-C30)cycloalkylene, preferably, each independently may be a single bond, a substituted or unsubstituted (C6-C18)arylene, or a substituted or unsubstituted (3- to 18-membered)heteroarylene, more preferably, each independently may be a single bond, a substituted or unsubstituted (C6-C12)arylene, or a substituted or unsubstituted nitrogen-containing (5- to 20-membered)heteroarylene.
  • L 1 and L 2 each independently may be a single bond, a substituted or unsubstituted phenylene, a substituted or unsubstituted o-biphenylene, a substituted or unsubstituted m-biphenylene, a substituted or unsubstituted p-biphenylene, a substituted or unsubstituted naphthylenylene, a substituted or unsubstituted triphenylene, a substituted or unsubstituted triazinylene, a substituted or unsubstituted quinoxalinylene, a substituted or unsubstituted quinazolinylene, or a substituted or unsubstituted benzoquinoxalinylene.
  • R 1 to R 5 each independently represent hydrogen, deuterium, halogen, cyano, a substituted or unsubstituted (C1-C30)alkyl, a substituted or unsubstituted (C6-C30)aryl, a substituted or unsubstituted (3- to 30-membered)heteroaryl, a substituted or unsubstituted (C3-C30)cycloalkyl, a substituted or unsubstituted (C1-C30)alkoxy, a substituted or unsubstituted tri(C1-C30)alkylsilyl, a substituted or unsubstituted di(C1-C30)alkyl(C6-C30) arylsilyl, a substituted or unsubstituted (C1-C30)alkyldi(C6-C30)arylsilyl, a substituted or un
  • R 1 to R 5 each independently may be hydrogen, deuterium, halogen, cyano, a substituted or unsubstituted (C1-C10)alkyl, a substituted or unsubstituted (C3-C10)cycloalkyl, or a substituted or unsubstituted (C1-C10)alkoxy, more preferably, may be hydrogen, deuterium, halogen, cyano, or a substituted or unsubstituted (C1-C4)alkyl.
  • all of R 1 to R 5 may be hydrogen.
  • a represents an integer of 1 to 4
  • c represents an integer of 1 or 2.
  • b represents an integer of 1 or more, preferably may be an integer of 1 to 20, or an integer of 1 to 14, more preferably, may be an integer of 1 to 8, or an integer of 1 to 6.
  • b may be an integer of 1 to 6
  • d and e each independently may be an integer of 1 to 4.
  • At least one of L 1 , L 2 , Ar1, and Ar2 may be a substituted or unsubstituted nitrogen-containing (5- to 30-membered)heteroaryl(ene), preferably, a substituted or unsubstituted nitrogen-containing (5- to 20-membered)heteroaryl(ene), more preferably, a substituted or unsubstituted nitrogen-containing (5- to 15-membered)heteroaryl(ene).
  • Ar1 and Ar2 each independently may be hydrogen, a substituted or unsubstituted (C6-C30)aryl, or a substituted or unsubstituted (3- to 30-membered)heteroaryl; L 1 and L 2 each independently may be a single bond, a substituted or unsubstituted (C6-C30)arylene, or a substituted or unsubstituted (3- to 30-membered)heteroarylene; preferably, Ar1 and Ar2 each independently may be hydrogen, a substituted or unsubstituted (C6-C18)aryl, or a substituted or unsubstituted (3- to 18-membered)heteroaryl; L 1 and L 2 each independently may be a single bond, a substituted or unsubstituted (C6-C18)arylene, or a substituted or unsubstituted (3- to 18-membered)heteroarylene
  • L 1 may be a single bond or a substituted or unsubstituted nitrogen-containing (5- to 20-membered)heteroarylene
  • Ar1 may be hydrogen, a substituted or unsubstituted (C6-C18)aryl, or a substituted or unsubstituted nitrogen-containing (5- to 20-membered)heteroaryl
  • L 2 may be a single bond or a substituted or unsubstituted (C6-C18)arylene
  • Ar2 may be hydrogen or a substituted or unsubstituted (C6-C18)aryl.
  • the compound represented by formula 1 may be more specifically illustrated by the following compounds, but is not limited thereto:
  • the compound of formula 1 according to the present disclosure may be produced by a synthetic method known to a person skilled in the art, and for example referring to the following reaction scheme 1, but is not limited thereto:
  • exemplary synthesis examples of the compounds represented by formula 1 are described, but they are based on Buchwald-Hartwig cross coupling reaction, N-arylation reaction, H-mont-mediated etherification reaction, Miyaura borylation reaction, Suzuki cross-coupling reaction, Intramolecular acid-induced cyclization reaction, Pd(II)-catalyzed oxidative cyclization reaction, Grignard reaction, Heck reaction, Cyclic Dehydration reaction, SN 1 substitution reaction, SN 2 substitution reaction, Phosphine-mediated reductive cyclization reaction, etc. It will be understood by one skilled in the art that the above reaction proceeds even if other substituents defined in the formula 1 other than the substituents described in the specific synthesis examples are bonded.
  • the present disclosure provides an organic electroluminescent device comprising the organic electroluminescent compound of formula 1.
  • the organic electroluminescent device includes a first electrode; a second electrode; and at least one organic layer interposed between the first electrode and the second electrode.
  • the organic layer may comprise at least one of the organic electroluminescent compound of formula 1.
  • the organic layer may further comprise at least one compound selected from the group consisting of an arylamine-based compound and a styrylarylamine-based compound.
  • the organic layer may further comprise at least one metal selected from the group consisting of metals of Group 1, metals of Group 2, transition metals of the 4 th period, transition metals of the 5 th period, lanthanides, and organic metals of the d-transition elements of the Periodic Table, or at least one complex compound comprising such a metal.
  • An organic electroluminescent material may be used as light-emitting materials for a white organic light-emitting device.
  • the white organic light-emitting device has suggested various structures such as a parallel side-by-side arrangement method, a stacking arrangement method, or CCM (color conversion material) method, etc., according to the arrangement of R (Red), G (Green), B (blue), or YG (yellowish green) light-emitting units.
  • the organic electroluminescent material according to one embodiment may also be applied to the organic electroluminescent device comprising a QD (quantum dot).
  • one of the first electrode and the second electrode may be an anode and the other may be a cathode.
  • the first electrode and the second electrode may each be formed as a transmissive conductive material, a transflective conductive material, or a reflective conductive material.
  • the organic electroluminescent device may be a top emission type, a bottom emission type, or a both-sides emission type according to the kinds of the material forming the first electrode and the second electrode.
  • the organic layer may comprise a light-emitting layer, and may further comprise at least one layer selected from a hole injection layer, a hole transport layer, a hole auxiliary layer, a light-emitting auxiliary layer, an electron transport layer, an electron injection layer, an interlayer, a hole blocking layer, an electron blocking layer, and an electron buffer layer.
  • a hole injection layer, a hole transport layer, an electron blocking layer, or a combination thereof can be used between the anode and the light-emitting layer.
  • the hole injection layer may be multi-layers in order to lower the hole injection barrier (or hole injection voltage) from the anode to the hole transport layer or the electron blocking layer, wherein each of the multi-layers may use two compounds simultaneously.
  • the hole injection layer may be doped as a p-dopant.
  • the electron blocking layer may be placed between the hole transport layer (or hole injection layer) and the light-emitting layer, and can confine the excitons within the light-emitting layer by blocking the overflow of electrons from the light-emitting layer to prevent a light-emitting leakage.
  • the hole transport layer or the electron blocking layer may be multi-layers, and wherein each layer may use a plurality of compounds.
  • An electron buffer layer, a hole blocking layer, an electron transport layer, an electron injection layer, or a combination thereof can be used between the light-emitting layer and the cathode.
  • the electron buffer layer may be multi-layers in order to control the injection of the electron and improve the interfacial properties between the light-emitting layer and the electron injection layer, wherein each of the multi-layers may use two compounds simultaneously.
  • the hole blocking layer or the electron transport layer may also be multi-layers, wherein each layer may use a plurality of compounds.
  • the electron injection layer may be doped as an n-dopant.
  • the light-emitting auxiliary layer may be placed between the anode and the light-emitting layer, or between the cathode and the light-emitting layer.
  • the light-emitting auxiliary layer When the light-emitting auxiliary layer is placed between the anode and the light-emitting layer, it can be used for promoting the hole injection and/or the hole transport, or for preventing the overflow of electrons.
  • the light-emitting auxiliary layer is placed between the cathode and the light-emitting layer, it can be used for promoting the electron injection and/or the electron transport, or for preventing the overflow of holes.
  • the hole auxiliary layer may be placed between the hole transport layer (or hole injection layer) and the light-emitting layer, and may be effective to promote or block the hole transport rate (or the hole injection rate), thereby enabling the charge balance to be controlled.
  • the hole transport layer which is further included, may be used as the hole auxiliary layer or the electron blocking layer.
  • the light-emitting auxiliary layer, the hole auxiliary layer, or the electron blocking layer may have an effect of improving the efficiency and/or the lifespan of the organic electroluminescent device.
  • a surface layer selected from a chalcogenide layer, a halogenated metal layer, and a metal oxide layer
  • a surface layer selected from a chalcogenide layer, a halogenated metal layer, and a metal oxide layer
  • a chalcogenide (including oxides) layer of silicon and aluminum is preferably placed on an anode surface of an electroluminescent medium layer
  • a halogenated metal layer or a metal oxide layer is preferably placed on a cathode surface of an electroluminescent medium layer.
  • the operation stability for the organic electroluminescent device may be obtained by the surface layer.
  • the chalcogenide includes SiO X (1 ⁇ X ⁇ 2), AlO X (1 ⁇ X ⁇ 1.5), SiON, SiAlON, etc.;
  • the halogenated metal includes LiF, MgF 2 , CaF 2 , a rare earth metal fluoride, etc.; and the metal oxide includes Cs 2 O, Li 2 O, MgO, SrO, BaO, CaO, etc.
  • a mixed region of an electron transport compound and a reductive dopant, or a mixed region of a hole transport compound and an oxidative dopant may be placed on at least one surface of a pair of electrodes.
  • the electron transport compound is reduced to an anion, and thus it becomes easier to inject and transport electrons from the mixed region to an electroluminescent medium.
  • the hole transport compound is oxidized to a cation, and thus it becomes easier to inject and transport holes from the mixed region to the electroluminescent medium.
  • the oxidative dopant includes various Lewis acids and acceptor compounds
  • the reductive dopant includes alkali metals, alkali metal compounds, alkaline earth metals, rare-earth metals, and mixtures thereof.
  • a reductive dopant layer may be employed as a charge generating layer to prepare an organic electroluminescent device having two or more light-emitting layers and emitting white light.
  • the organic electroluminescent compound of formula 1 may be comprised in the light-emitting layer.
  • the organic electroluminescent compound of formula 1 may be comprised as a host material.
  • the light-emitting layer may further contain at least one dopant, and if necessary, may further contain a compound other than the organic electroluminescent compound of formula 1 of the present disclosure as a second host material.
  • the weight ratio of the first host material to the second host material is in the range of 1:99 to 99:1.
  • the second host material may use any well-known phosphorescent host.
  • the dopant comprised in the organic electroluminescent material of the present disclosure may be at least one phosphorescent or fluorescent dopant, preferably a phosphorescent dopant.
  • the phosphorescent dopant material applied to the organic electroluminescent device of the present disclosure is not particulary limited, but may be preferably a metallated complex compound(s) of a metal atom(s) selected from iridium (Ir), osmium (Os), copper (Cu), and platinum (Pt), more preferably an ortho-metallated complex compound(s) of a metal atom(s) selected from iridium (Ir), osmium (Os), copper (Cu), and platinum (Pt), and even more preferably ortho-metallated iridium complex compound(s).
  • the compound represented by the following formula 101 may be used as the dopant, but is not limited thereto:
  • L is selected from the following structure 1 or 2:
  • R 100 to R 103 each independently represent hydrogen, deuterium, halogen, halogen-substituted or unsubstituted (C1-C30)alkyl, a substituted or unsubstituted (C3-C30)cycloalkyl, a substituted or unsubstituted (C6-C30)aryl, cyano, a substituted or unsubstituted (3- to 30-membered)heteroaryl, or a substituted or unsubstituted (C1-C30)alkoxy; or R 100 to R 103 may be linked to an adjacent substituent(s) to form a substituted or unsubstituted fused ring, e.g., a substituted or unsubstituted quinoline, a substituted or unsubstituted benzofuropyridine, a substituted or unsubstituted benzothienopyridine, a substituted or unsubstituted indenopyridine,
  • R 104 to R 107 each independently represent hydrogen, deuterium, halogen, halogen-substituted or unsubstituted (C1-C30)alkyl, a substituted or unsubstituted (C3-C30)cycloalkyl, a substituted or unsubstituted (C6-C30)aryl, a substituted or unsubstituted (3- to 30-membered)heteroaryl, cyano, or a substituted or unsubstituted (C1-C30)alkoxy; or R 104 to R 107 may be linked to an adjacent substituent(s) to form a substituted or unsubstituted fused ring, e.g., a substituted or unsubstituted naphthyl, a substituted or unsubstituted fluorene, a substituted or unsubstituted dibenzothiophene, a substituted or unsubstituted dibenzofur
  • R 201 to R 211 each independently represent hydrogen, deuterium, halogen, halogen-substituted or unsubstituted (C1-C30)alkyl, a substituted or unsubstituted (C3-C30)cycloalkyl, or a substituted or unsubstituted (C6-C30)aryl; or may be linked to an adjacent substituent(s) to form a substituted or unsubstituted fused ring; and
  • s represents an integer of 1 to 3.
  • the specific examples of the dopant compound include the following, but are not limited thereto:
  • each layer of the organic electroluminescent device of the present disclosure dry film-forming methods such as vacuum evaporation, sputtering, plasma, ion plating methods, etc., or wet film-forming methods such as ink jet printing, nozzle printing, slot coating, spin coating, dip coating, flow coating methods, etc., can be used.
  • dry film-forming methods such as vacuum evaporation, sputtering, plasma, ion plating methods, etc.
  • wet film-forming methods such as ink jet printing, nozzle printing, slot coating, spin coating, dip coating, flow coating methods, etc.
  • co-evaporation or mixture-evaporation may be used, but is not limited thereto.
  • a thin film may be formed by dissolving or diffusing materials forming each layer into any suitable solvent such as ethanol, chloroform, tetrahydrofuran, dioxane, etc.
  • the solvent may be any solvent where the materials forming each layer can be dissolved or diffused, and where there are no problems in film-formation capability.
  • the co-deposition is a mixed deposition method in which two or more isomer materials are put into respective individual crucible sources and a current is applied to both cells simultaneously to evaporate the materials and to perform mixed deposition; and the mixed deposition is a mixed deposition method in which two or more isomer materials are mixed in one crucible source before deposition, and then a current is applied to one cell to evaporate the materials.
  • the organic electroluminescent device of the present disclosure can be used for the manufacture of display devices such as smartphones, tablets, notebooks, PCs, TVs, or display devices for vehicles, or lighting devices such as outdoor or indoor lighting.
  • 9-bromophenanthrene 50 g, 194.4 mmol was dissolved in 1300 mL of THF (Tetrahydrofuran) in flask, and at -78°C, n- butyllithium (97 mL, 194.4 mmol, 2.0 M in Hexane) was added slowly to the flask. After one hour, triisopropylborate (89 mL, 388.8 mmol) was added to the flask and stirred at room temperature for 12 hours, and then distilled water was added. After completion of the reaction, the organic layer was extracted with ethylacetate, and the residual water was removed with magnesium sulfate followed by drying, and then distillation under reduced pressure. Next, compound 1-1 was obtained (33.9 g, yield: 78%) by recrystallization with ethyl acetate and hexane.
  • THF Tetrahydrofuran
  • An OLED device comprising the compound of the present disclosure was produced.
  • a transparent electrode indium tin oxide (ITO) thin film (10 ⁇ /sq) on a glass substrate for an OLED device (GEOMATEC CO., LTD., Japan) was subjected to an ultrasonic washing with acetone, ethanol, and distilled water, sequentially, and then was stored in isopropanol.
  • the ITO substrate was then mounted on a substrate holder of a vacuum vapor deposition apparatus.
  • Compound HI-1 was introduced into a cell of the vacuum vapor deposition apparatus, and then the pressure in the chamber of the apparatus was controlled to 10 -6 torr.
  • compound HI-2 was introduced into another cell of the vacuum vapor deposition apparatus, and was evaporated by applying an electric current to the cell, thereby forming a second hole injection layer having a thickness of 5 nm on the first hole injection layer.
  • Compound HT-1 was then introduced into another cell of the vacuum vapor deposition apparatus, and was evaporated by applying an electric current to the cell, thereby forming a first hole transport layer having a thickness of 10 nm on the second hole injection layer.
  • Compound HT-2 was then introduced into another cell of the vacuum vapor deposition apparatus, and was evaporated by applying an electric current to the cell, thereby forming a second hole transport layer having a thickness of 60 nm on the first hole transport layer.
  • a light-emitting layer was formed thereon as follows: Compound H-1 (Device Example 1) or H-56 (Device Example 2) of the following Table 1 was introduced into one cell of the vacuum vapor depositing apparatus as a host, and compound D-39 was introduced into another cell as a dopant.
  • the two host materials were evaporated at a different rate and the dopant was deposited in a doping amount of 3 wt%, to form a light-emitting layer having a thickness of 40 nm on the hole transport layer.
  • compounds ET-1 and EI-1 were evaporated at a rate of 1:1, and were deposited to form an electron transport layer having a thickness of 35 nm on the light-emitting layer.
  • an Al cathode having a thickness of 80 nm was deposited on the electron injection layer by another vacuum vapor deposition apparatus.
  • an OLED was produced.
  • OLEDs were produced in the same manner as in Device Example 1, except that compound CBP (Comparative Example 1) or compound X (Comparative Example 2) was used as the host of the light-emitting layer, respectively.
  • the OLEDs of Device Examples 1 and 2 using the organic electroluminescent compound according to one embodiment as a host exhibit far superior effects in terms of driving voltage, luminous efficiency, and lifespan, as compared with the OLED of Comparative Example 1 using a conventional host material such as CBP.
  • the OLED of Comparative Example 2 uses compound X having indolocarbazole derivatives as a basic skeleton; however, it is significantly lower than the OLED according to the Device Examples in terms of luminous efficiency and lifespan.
  • the compound X is indolo[2,3-a]carbazole as a basic skeleton, wherein as the N-N distance of indolocarbazole is nearer, the electron mobility is slowed due to the steric hindrance between LUMO and the phenyl ring of phenanthrene fused to its terminal, resulting in a decrease in the efficiency and lifespan of the device.
  • the organic electroluminescent device comprising the organic electroluminescent compound according to the present disclosure has low driving voltage, high luminous efficiency, and significantly improved lifespan characteristics as compared with the organic electroluminescent device comprising the conventional organic electroluminescent compound.

Abstract

La présente invention concerne un composé électroluminescent organique et un dispositif électroluminescent organique le comprenant. En intégrant le composé électroluminescent organique, un dispositif électroluminescent organique ayant une faible tension de commande et/ou un rendement lumineux élevé et/ou une longue durée de vie peut être obtenu.
PCT/KR2019/006700 2018-06-05 2019-06-04 Composé électroluminescent organique et dispositif électroluminescent organique le comprenant WO2019235803A1 (fr)

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